David Letterman Reflects on 33 Years in Late-Night Television

Slide Show | Letterman Prepares to Sign Off A look backstage at the “Late Show” as David Letterman nears the end of his more than 33 years in late-night television.

Damon Winter / The New York Times

By DAVE ITZKOFF

April 29, 2015

In a single bound, David Letterman seemed to leap the full length of the stage at the Ed Sullivan Theater, racing from backstage as if he’d been thrust forward by the fanfare played by his longtime bandleader, Paul Shaffer, and his CBS Orchestra, and by the rumble of his announcer, Alan Kalter, bellowing his name — “Daaaaay-vid Leh-terrrr-maaaaaaaan!”

It was a routine Mr. Letterman, 68, has performed countless times but will repeat no more after May 20, when he will preside over his last episode of “Late Show,” the CBS franchise he established and has hosted since 1993. Like the veteran slugger who comes to the ballpark for batting practice, he was here on this April afternoon partly to warm up his swing on a few easy pitches, but mostly to put on a show.

No home viewers were watching as he twirled his microphone around like a Wild West lasso, walked it across the floor like a dog and leaned on an expensive broadcast camera. This was a pretaping ritual Mr. Letterman was doing only for the few hundred audience members in the theater. Or maybe he was doing it only for himself.

“Everything O.K. at home?” he asked the crowd. “Everything O.K. at work?” Met with mostly cheers, he laughed and added: “You don’t find yourself filled with some kind of emotional longing? Are we emotionally stable?”

But how could these fans not be riddled with angst, knowing that in a few weeks, Mr. Letterman would bid a heartfelt good night to all of this, after a run of more than 33 years in late-night television — even longer than the three-decade tenure of his mentor, Johnny Carson. After that last show, he will head home to his wife, Regina, and 11-year-old son, Harry, and try to figure out what comes next.

With almost no blueprint to follow, Mr. Letterman showed that late-night TV could offer more than a what’s-in-the-news monologue and witty banter with celebrity guests (though he was capable of doing all that, as well). He made his show a home for misfits and oddballs, for Andy Kaufman’s slap fights and Larry (Bud) Melman’s shrill soliloquies, where champion bird callers or his own mother were deemed as important as Hollywood ingénues or rising rock bands.

Mr. Letterman proved he could reinvent himself, too: When he was passed over as Mr. Carson’s heir in favor of Jay Leno, he packed up for the uncharted territory of CBS and became a more inclusive — if still idiosyncratic — master of ceremonies.

But Mr. Letterman is leaving a late-night biosphere very different from the one he helped thrive. Hosts like Jimmy Fallon (who ultimately replaced Mr. Leno at “Tonight”) and Jimmy Kimmel (at ABC’s “Jimmy Kimmel Live”) are dominating with their own ingenious energy, their Internet savvy and their visible youth, and Mr. Letterman is about to be replaced by Stephen Colbert, the politically astute smart aleck of “The Colbert Report.”

Not that any of these issues appeared to be on Mr. Letterman’s mind during his preshow set. Asked by an audience member from Newberg, Ore., if he had any advice for that city’s impending graduates, Mr. Letterman replied, “Treat a lady like a whore, and a whore like a lady.” After some laughter at this seemingly un-Letterman-like joke, the host chuckled to himself and said: “I don’t know why I would say something like that.”

“What do you care?” Mr. Shaffer said.

But no matter how hard he has tried to hide it over the years, Mr. Letterman does care. As he said, more sincerely, to the man who had asked for graduation advice, “If you do good things for people, it will never stop making you feel good about yourself.”

Upstairs in his “Late Show” offices a few hours later, a contemplative Mr. Letterman emerged, dressed in khakis and a T-shirt that said “Genetically Engineered Trout Is Safe!” to reflect on all that he has learned along the way. In these edited excerpts from that conversation, he offered his unguarded and unsparing assessments of his heroes, his colleagues, his would-be successors and himself.

Q. As your last show approaches, have there been times when you’ve thought: I’m leaving too soon?

A. Yeah, I’m awash in melancholia. Over the weekend, I was talking to my son, and I said, “Harry, we’ve done like over 6,000 shows.” And he said, [high-pitched child’s voice] “That’s creepy.” And I thought, well, in a way, he’s right. It is creepy. Every big change in my life was full of trepidation. When I left Indiana and moved to California. When Regina and I decided to have a baby — enormous anxiety and trepidation. Those are the two biggest things in my life, and they worked out beyond my wildest dreams. I’m pretending the same thing will happen now. I’ll miss it, desperately. One of two things: There will be reasonable, adult acceptance of transition. Or I will turn to a life of crime.

In the time since you made your announcement, the consensus is that you seem more relaxed and the show feels looser. Is that how you see it?

I couldn’t make that observation, but I certainly feel it. Because I think there’s a difference between regular-season hockey and playoff hockey. And I’m not in the playoffs. Yeah, I do notice a difference. When I was watching those interim shows they did on “The Late Late Show,” and I saw John Mayer hosting one night, I thought, “Ohhhh, now I see exactly what the problem is.” Because he’s young. He’s handsome. He’s trim. He’s witty. He was comfortable. So then I realized, I got nothing to worry about. I know I can’t do what Jimmy Fallon’s doing. I know I can’t do what Jimmy Kimmel is doing. There’s nothing left to be worried about. It’s all over, Dad, you’re going to be just fine. You’re going to a new place. They’ll be very nice to you, Dad. You’ll make a lot of friends.

David Letterman dressing for a taping of “Late Show.” Each cup to the left represents a completed show.

Damon Winter / The New York Times

The late-night TV landscape has changed so much in the time you’ve been on the air. Do you think you’ve left a lasting impact on it?

I see that things are certainly different. A lot of what we did was dictated by Carson. A guy named Dave Tebet, who worked for NBC and was like a talent liaison — in the same that way that Al Capone was a beverage distributor — he came to us and he said: “You can’t have a band. You can have a combo. You can’t do a monologue. You can’t do, like, Aunt Blabby. You can’t do Tea Time Movie Matinee.” There were so many restrictions. So that was the framework we were handed, which was fine, because then they gave us an excuse not to think of that thing to do.

You were innovating out of necessity?

I never knew if the stupider things we did or the more traditional things we did would work. I didn’t know if the stupid stuff would alienate people. I didn’t know if the traditional stuff would be more appealing. And then, when I look back on it now, of course the answer is, you want to do the weird thing.

Did the ascent of hosts like Jimmy Fallon and Jimmy Kimmel push you out of the job?

No, they didn’t push me out. I’m 68. If I was 38, I’d probably still be wanting to do the show. When Jay was on, I felt like Jay and I are contemporaries. Every time he would get a show at 11:30, he would succeed smartly. And so I thought, This is still viable — an older guy in a suit. And then he left, and I suddenly was surrounded by the Jimmys.

It seems like there’s an increasing emphasis, at least with your network competitors, to create comedy bits that will go viral on the Internet. Did you make a conscious choice to stay out of that arms race?

No, it just came and went without me. It sneaked up on me and went right by. People on the staff said, “You know what would be great is if you would join Twitter.” And I recognized the value of it. It’s just, I didn’t know what to say. You go back to your parents’ house, and they still have the rotary phone. It’s a little like that.

Did you have any involvement in choosing Stephen Colbert as your successor?

No. Not my show. When we sign off, we’re out of business with CBS. I always thought Jon Stewart would have been a good choice. And then Stephen. And then I thought, well, maybe this will be a good opportunity to put a black person on, and it would be a good opportunity to put a woman on. Because there are certainly a lot of very funny women that have television shows everywhere. So that would have made sense to me as well.

But you were not consulted?

[shakes head no] Mm-mmm.

Did that bother you?

Yeah, I guess so. Just as a courtesy, maybe somebody would say: “You know, we’re kicking around some names. Do you have any thoughts here?” But it doesn’t bother me now. At the time, I had made the decision [to leave] and I thought, O.K., this is what comes when you make this decision.

Their selection of Stephen Colbert came very quickly.

They didn’t have to put much thought to it, did they? I think it was the very next day. [laughs] But if you’re running the show with Jimmy Fallon, that’s a certain dynamic. Jimmy Kimmel, a completely different dynamic. And now Stephen Colbert will add a third, different dynamic to it. I think it will be very interesting to see what he will do.

Have you offered him any advice on how he should run his show?

No. We chatted when the announcement was made. And that was about it. I don’t think he needs — he’s not a kid. He’s not a beginner. He’s had pretty good success.

You’ve often talked about Johnny Carson as a mentor and a creative hero. Do you feel you’ve lived up to his standard?

Whenever I see clips from his old show, I’m reminded of what I always knew about him, which is that the highs and lows on that show are just about like that: [moves his hand in a straight line] There are funny moments, but he doesn’t lose control. If things aren’t going well, that’s fine, too. There’s a consistency about his presence that is very satisfying. I never felt that way. I always felt like [panting heavily] “We’ve got to do this, and we’ve got to do that.” Carson, whether he knew it or not, was doing exactly what TV is supposed to be. Just let it go. Because it’s 11:30, and people are just looking for a pleasant experience. And I wish I could do that.

You don’t think you can be that relaxed?

I think now, more than ever. But certainly not in the beginning. When we got a show on right after Carson, I’m thinking, Oh, God, I’m going to be compared to Carson back-to-back. And then when we went head-to-head with Jay, I never had the confidence. But now that the consequences have disappeared, yeah, what do I care? At some point, all of a sudden, people in show business that I never knew before would say to me on the show, “Oh, it’s such an honor to be here.” And I would think, What are you talking about? It’s just a goddamn TV show. And then I realized, this is what happens when you get to be older and you’ve been around for a while, people succumb to this artificial reverence. It was always kids that had only been in show business a couple of years. I just thought, Oh. I know. Your grandparents used to watch.

You don’t think their praise was sincere?

I’m sure it was sincere. But it was artificially generated. The same thing happened to me. I can remember sitting next to Johnny Carson for the first time, and I’m thinking, Holy God, this is like looking at Abraham Lincoln. You’ve seen him forever on the $5 bill. And now all of a sudden he’s here. And that was too much for me. I’m not saying it happened in like measurement, but I understand the dynamic.

When you moved to CBS, so much was made of your rivalry with Jay Leno. In retrospect, do you feel like this was overblown?

No, I don’t think so. It would have happened if I’d have gotten the “Tonight” show, and he would have come here. I think people are curious to see, well, what will happen? And we prevailed for a while, and then I lost my way a little bit. Quite a little bit. And at that point, there was not much I could do about it. People just liked watching his show more than they liked watching my show.

Mr. Letterman reviewing cue cards with Todd Seda.

Damon Winter / The New York Times

You feel that something, philosophically, at your show, caused this viewership shift?

Yeah. And it’s just my judgment. Before, I felt pretty confident in what we were up to, because there was no competition to speak of, whatsoever. In the beginning [at CBS], we came out of the chute, going a million miles an hour. And then when that was all done, we just sort of said, “Really, can we go a million miles an hour again?” And we tried, and we couldn’t. I think we had gone way down the road, maybe way down the wrong road.

How did you get back on the right track?

I don’t know that we ever did get back the right way. It didn’t start to settle down until it couldn’t be more clear that Jay was the more popular show. And when we all realized that there’s not much we can do here — you can’t put toothpaste back in the tube — then we started going our own way again. I think it was just inevitability. The guy in the race who spends more time looking over his shoulder, well, that’s the mistake. For two years, I made that mistake. We ran out of steam.

But you came in and continued to do the job.

Well, that was the other thing. I was always surprised that they didn’t let me go. Wait a minute — wouldn’t you like me to go home now? Well, no. Next thing you know, I’ve been here 23 years.

Were there times in your CBS tenure when you thought you might not have control over when you’d leave?

It’s a blur to me now, but when we came over from NBC, it was Howard Stringer running the show. He brought us here, and paid a lot of money to remodel this theater and really made the commitment. And then when he left, that commitment, I was worried about that leaving, too. Those were the days when CBS was really doing poorly. They lost [N.F.L.] football. And I just thought to myself, this can’t be good for us. Then [Les] Moonves came in and turned the place into Disney World.

I was concerned that I’ll never be able to run again — that was my big concern. Because I had so relied on running, all my life, to get myself clearheaded. And of course, I was worried that somebody would go on while I was off with my heart surgery, and be good enough that they didn’t want me back. As I’m trying to recover from quintuple bypass surgery, I’m paranoid that my life is ending. And then, six weeks after the surgery, I ran for five miles. So let’s face it, I am a hero. There’s no two ways of looking at it.

What about in 2009, when you revealed that you were the target of an extortion attempt stemming from your sexual relationships with female staffers?

Oh, yes. My sex scandal. That’s right.

Did you think that was going to be the end of your career?

Looking at it now, yes, I think they would have had good reason to fire me. But at the time, I was largely ignorant as to what, really, I had done. It just seemed like, O.K., well, here’s somebody who had an intimate relationship with somebody he shouldn’t have had an intimate relationship with. And I always said, “Well, who hasn’t?” to myself. But then, when I was able to see from the epicenter, the ripples, I thought, yeah, they could have fired me. But they didn’t. So I owe them that.

Did you think people were surprised to hear you talk about these matters so candidly?

I didn’t know what else to do. I couldn’t think of a really good lie.

How do you feel about your reputation that you simply aren’t a warm person?

I understand that. I think it’s genetic. I don’t want to blame it on my parents and my grandparents. But you don’t need to be all that warm when you’re born and raised in Linton, Ind., and working in a coal mine. They weren’t hiring coal miners on the basis of their personalities. Inside, I feel like everything’s firing properly. And then when I look at a videotape, I just think, What the hell is Dave [angry] about? When in fact I’m not [angry]. We used to do that with my mom. We’d say, “Mom, are you all right?” Because she’d sit there looking dour. And she’d say [shouting], “I’m fine!” It’s the Golden Rule. I try to be nice to people who are nice to me. I like doing nice things for people. It makes me feel good. But I think it’s legitimate.

It’s a fair assessment?

Let’s blame Jack Paar. Years and years and years ago, before the late-night shows, he said to me [whispery Jack Paar voice]: “You know what, pal? It’s O.K. to let people know you’re upset about things.” And so I thought, well, maybe there’s some wisdom to that. I might have used that to my own disadvantage, sometimes.

Has doing the show taught you how much of yourself to give to an audience?

Absolutely right. In the beginning, you think, I can’t wait to get on television. I’m going to straighten it out. Then people will be saying, “God bless you, Dave Letterman, we have been waiting for somebody to take care of television.” That’s how you feel. And now, I don’t feel that way.

Have you decided what you’ll do in your very last show?

I have decided what I will do, yes. And I know of other things that are being worked on. My only concern is mine. What will I do? And I now know exactly what I will do.

That was fantastic. I can remember when he signed off that night, it just left you [with] a nagging sense of loss. This doesn’t apply here. I want it to be a little more cheery. And I want it to be upbeat, and I want it to be funny, and I want people to be happy that they spent the time to watch it. Of course, Johnny’s last show was historic. This one won’t be. [laughs] This one, people will say: “Ah, there you go. When’s the new guy starting?”

Even though you won’t be on CBS at 11:35 p.m. anymore, do you think you might come back in another form fairly quickly?

It just depends on the number of bridges I’ve burned. I don’t know how long this has been going on, but Jane Pauley is now on the CBS “Sunday Morning” show. Perfect fit. So I thought, by God, good for Jane. That’s a lovely thing for her to have now. So maybe one day, something of that level will happen to me.

The last “Late Show” airs on a Wednesday. What will you do Thursday morning?

I will be completely in the hands of my family. I will be going, later in the month, to the Indianapolis 500. And then beyond that, for the first time since Harry’s been alive, our summer schedule will not be dictated by me. It will be entirely dictated by what my son wants to do. And I think that’s pretty good. After you take a good, solid punch to the head, you’re just a little wobbly. I think in that state it would be good to have others making my decisions. That’s how he’s describing his retirement. A good solid punch to the head.